P-t-octylphenyl



United States Patent Ofi ice 3,126,409 Patented Mar. 24, 1964 This invention generally relates to, and has for its object the provision of a class of new and useful chemical compounds.

More particularly, this invention relates to compounds of the Formula I:

wherein R and R" are as hereinbefore defined yields an intermediate aryl S-resorcylate. The esterification may be conducted in the presence of a condensation reagent such as phosphorous oxychloride or polyphosphoric acid.

Suitable phenols for this purpose are inter alia:

p-Octylphenol m-Amylphenol p-Nonylphenol p-Dodecylphenol p-Isoamylphenol o-Isoamylphenol p-Sec-butylphenol o-Sec-butylphenol p-Tert.-amylphenol o-Sec-amylphenol o-t-Butylphenol o-Chlorophenol 4methoxyphenol o-n-Butylphenol p-n-Butylphenol p-Cyclohexylphenol o-Cyclohexylphenol o-Cyclopentylphenol p-Cyclopentylphenol 2-t-butyl-4-methylphenol p-tert.-butylphenol p-Chlorophenol 2,4-dichlorophenol p Bromophenol 3,4-dichlorophenol 3-methoxyphenol 3,4-dimethoxyphenol The compounds thus prepared may be alkylated to yield the compounds of Formula I wherein R is alkyl as above described. The alkylation is conveniently conducted in a solvent medium with an alkyl halide in the presence of an acid acceptor such as potassium carbonate, pyridine or triethanolamine. Suitable alkylating agents are alkyl iodides and bromides of from one to eighteen carbon atoms such as methyl iodide, ethyl iodide, butyl bromide, hexyl iodide, dodecyl bromide and octadecyl bromide including both straight and branched chain derivatives.

The compounds of Formula I are useful as intermediates for chemical reactions, as sunburn preventatives and as additives for the stabilization of polymeric materials, e.g. polyolefins such as polyethylene and polypropylene.

This invention may be further illustrated by the following examples in which parts are by weight unless otherwise stated.

fi-Resorcylic acid (15.4 parts), p-(t-octyl)-phenol (20.6 parts) and phosphorous oxychloride (30. 6 parts) are stirred and heated at C. for 30 minutes. The mixture is cooled and drowned in water and a solid forms. The solid is recrystallized from methylcyclohexane. Melting point 166-167 C.

When either dodecylphenol (26.2 parts) or nonylphenol (22.0) parts is used in place of the p-t-octylphenol in the above example, the corresponding dodecylphenyl fl-resorcylate or nonylphenyl B-resorcylate is respectively obtained.

Example 2 154 parts of li-resorcylic acid and 150 parts of p-tertbutylphenol are blended together and added portionwise to 300 parts of polyphosphoric acid preheated on a steam bath. After heating for 30 minutes the paste is cooled in an ice-Water bath and drowned in 1,000 parts of water. The mixture is heated for one hour on a steam bath and cooled. The product is recrystallized from toluene giving crystals (M.P. 158158.5 C.).

When 176 parts of p-cyclohexylphenol or 112 parts of p-chlorophenol is used in place of the p-tert-butylphenol in the above example, the corresponding p-cyclohexylphenyl B-resorcylate or p-chlorophenyl B-resorcylate is obtained.

(IIIH p-Chlorophenyl ,B-resorcylate (200 parts), n-butyl bromide (137 parts), potassium carbonate (158 parts), potassium iodide (2 parts) and acetone 1000 parts are refluxed 10 hours. The mixture is drowned with water, and the product filtered and recrystallized.

Example 5 4-O-n-octyl-13-resorcylic acid (266 parts), 4-n-octyloxyphenol (222 parts) and phosphorous oxychloride (306 parts) are heated at C. for 30 minutes. The mixture is drowned in water, and the resulting product is recrystallized.

3 4 Example 6 References Cited in the file of this patent 03 UNITED STATES PATENTS HO 2,126,179 Duggan Aug. 9, 1938 5 2,464,250 M011 et a1 Mar. 15, 1949 0 OCH 2,858,293 Clark et a1 Oct. 28, 1958 3 B-Resorcylic acid (154 parts), m-hydroxy anisole (123 OTHER REFERENCES parts) and phosphorous oxychloride (306 parts) are Hirwe et a1.: Chem. Abstracts, volume 49, pages 10887,

stirred and heated at 125 C. for 30 minutes. The mix- 14684 (1955). ture is cooled and drowned in Water. The product is re- 10 crystallized.

I claim:

The compound p-t-octylphenyl fi-resorcylate. 

